Synthesis, Spectral-Luminescent Properties of B(III)
and Zn(II) Complexes with Alkyl- and Aryl-Substituted
Dipyrrins and Azadipyrrins

E. V. Antina^a, M. B. Berezin^a, N. A. Dudina^a, S. L. Burkova^a, and A. Yu. Nikonova^b

^a Krestov Institute of Solution Chemistry, Russian Academy of Sciences,
Akademicheskaya ul. 1, Ivanovo, 153045 Russia

e-mail: nad@isc-ras.ru

^b Ivanovo State University of Chemistry and Technology,
Sheremetevskii pr. 7, Ivanovo, 153000 Russia

Received November 25, 2013

Abstract—Effect of complexing atom, molecular structure of dipyrrolylmethene and its aza analog on spectral-
luminescent properties of heteroleptic boron(III) and homoleptic zinc(II) complexes with 3,3',5,5'-tetramethyl-
2,2'-dipyrrolylmethene, 3,3',5,5'-tetraphenyl-2,2'-dipyrrolylmethene, and 3,3',5,5'-tetraphenyl-ms-aza-2,2'-
dipyrrolylmethene in organic solvent solutions was studied. The complexes were found to exhibit strong chro-
mophore ( = 350–690 nm, ~ 10⁵ L/mol cm) and fluorescent properties. Quantum yield (^fl) for fluoroborate
complexes reaches 100% and is weakly dependent on medium nature. The value of ^fl for phenyl- and alkyl-
substituted zinc(II) dipyrrolylmethenates in nonpolar solvents is not higher 0.3 and 0.03, respectively; complete
fluorescence quenching is observed in electron-donating solvents. Aza-substitution at the meso spacer causes
considerable shift of electronic absorption and fluorescence spectra to the red region but completely quenches
fluorescence of zinc(II) chelates and decreases ^fl of boron(III) complex to 0.04.

DOI: 10.1134/S0036023614100027

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